Showing Compound Vanillic acid (FDB000846)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:44 UTC

Update date

2024-11-29 22:27:57 UTC

Primary ID

FDB000846

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Vanillic acid

Description

Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5'nucleotidase activity. (PMID: 16899266).

CAS Number

121-34-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
4-Hydroxy-3-methoxybenzoic acid	ChEBI
4-Hydroxy-3-methoxybenzoate	Kegg
Vanillate	Generator
3-Methoxy-4-hydroxybenzoate	HMDB
3-Methoxy-4-hydroxybenzoic acid	HMDB
4-Hydroxy-3-methoxy-benzoate	HMDB
4-Hydroxy-3-methoxy-benzoic acid	HMDB
4-Hydroxy-m-anisate	HMDB
4-Hydroxy-m-anisic acid	HMDB
Acide vanillique	HMDB
p-Vanillate	HMDB
p-Vanillic acid	HMDB
Protocatechuic acid 3-methyl ester	HMDB
Acid, 4-hydroxy-3-methoxybenzoic	HMDB
p Hydroxy m methoxy benzoic acid	HMDB
4 Hydroxy 3 methoxybenzoic acid	HMDB
Acid, vanillic	HMDB
Acid, p-hydroxy-m-methoxy-benzoic	HMDB
p-Hydroxy-m-methoxy-benzoic acid	HMDB
2-Methoxy-4-carboxyphenol	HMDB
Methylprotocatechuic acid	HMDB
VA	HMDB
m-Methoxy-p-hydroxy-benzoic acid	HMDB
Vanillic acid	KEGG
4 Hydroxy 3 methoxybenzoic Acid	biospider
4-hydroxy-3-methoxy-Benzoate	biospider
4-hydroxy-3-methoxy-Benzoic acid	biospider
4-Hydroxy-3-methoxybenzoic acid (vanillic acid)	biospider
4-hydroxy-m-Anisate	biospider
4-hydroxy-m-Anisic acid	biospider
Acid, 4-Hydroxy-3-methoxybenzoic	biospider
Benzoic acid, 4-hydroxy-3-methoxy-	biospider
m-Anisic acid, 4-hydroxy-	biospider
P hydroxy m methoxy benzoic acid	biospider
P-hydroxy-m-methoxy-benzoic acid	biospider
P-hydroxy-m-methoxy-benzonic acid	biospider
P-vanillate	biospider
P-vanillic acid	biospider
Protocatechuic acid, 3-methyl ester	biospider
Va (van)	biospider
VNL	biospider

Predicted Properties

Property	Value	Source
Water Solubility	5.7 g/L	ALOGPS
logP	1.7	ALOGPS
logP	1.17	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.76 m³·mol⁻¹	ChemAxon
Polarizability	15.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H8O4

IUPAC name

4-hydroxy-3-methoxybenzoic acid

InChI Identifier

InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)

InChI Key

WKOLLVMJNQIZCI-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(O)C=CC(=C1)C(O)=O

Average Molecular Weight

168.148

Monoisotopic Molecular Weight

168.042258738

Classification

Description

Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

M-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Benzoic acid
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:30816 )
methoxybenzoic acid (CHEBI:30816 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Microbe:

Amycolatopsis

Pseudomonas:

Delftia:

Delftia acidivorans

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 57.14%; H 4.80%; O 38.06%	DFC
Melting Point	Mp 210°	DFC
Boiling Point	Not Available
Experimental Water Solubility	1.5 mg/mL at 14 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	1.43	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 9.39 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0gb9-6900000000-c13506201c3612fc7ca5	2015-03-01	View Spectrum
GC-MS	Vanillic acid, 2 TMS, GC-MS Spectrum	splash10-0hp2-2691000000-8409d9c758b023c6576b	Spectrum
GC-MS	Vanillic acid, non-derivatized, GC-MS Spectrum	splash10-0gb9-2900000000-ccd8d4a214bc1a7f08c5	Spectrum
GC-MS	Vanillic acid, non-derivatized, GC-MS Spectrum	splash10-0hp2-2691000000-8409d9c758b023c6576b	Spectrum
GC-MS	Vanillic acid, non-derivatized, GC-MS Spectrum	splash10-0g0b-2981000000-a58243e35d1e3a64d2aa	Spectrum
Predicted GC-MS	Vanillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0g4i-1900000000-851f4a1738be8dd91d47	Spectrum
Predicted GC-MS	Vanillic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dj-7390000000-18c5f822b380ea00aa26	Spectrum
Predicted GC-MS	Vanillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vanillic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vanillic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vanillic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vanillic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vanillic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0gb9-0900000000-0aa6709c16899e222086	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-0900000000-9aa2b9d4aa89e6ac12ab	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-0900000000-6d98ebfa89f4b8ee1e6b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0gb9-2900000000-babed327a6e49c6f7d51	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-105f33777cee542cf6df	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-05fr-1900000000-a502792703fa2f211035	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4l-5900000000-037ef32f4c68a5252b92	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9800000000-ecd60ac022f5fee1d5ef	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-066u-9300000000-c63f7f792794f3c748a0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0923211100-7e9f357f7429cff05524	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0923211100-7e9f357f7429cff05524	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0429110000-57f8760ce65d48cdc01f	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0429110000-57f8760ce65d48cdc01f	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0923211100-7e9f357f7429cff05524	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0a4i-0900000000-8e112ffa4dcc7c08b0fd	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0429110000-57f8760ce65d48cdc01f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0uxr-0900000000-29a2674dccd1fa478bd5	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-105f33777cee542cf6df	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-05fr-1900000000-c4ce596998934098267b	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-342964fa3647815dd1d2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uxr-0900000000-f16c365899f9d95733d3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfs-5900000000-e5593db0a935e1534bc6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-6a1a2db582acd95348ea	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0600-0900000000-eda6cfe601d63ed00f8d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-6900000000-b2c1e3f6b255e94a10af	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Phenol-Explorer ID

DrugBank ID

HMDB ID

CRC / DFC (Dictionary of Food Compounds) ID

BJS05-K:BJS01-G

EAFUS ID

3829

Dr. Duke ID

4-HYDROXY-3-METHOXY-BENZOIC-ACID|VANILLIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00002682

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1051611

SuperScent ID

Not Available

Wikipedia ID

Phenol-Explorer Metabolite ID

414

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Allelopathic		Biochemicals that inhibit growth, survival, or reproduction in other organisms, with potential therapeutic applications in weed control, antimicrobial, and anticancer treatments, and key medical uses in developing novel pesticides, antibiotics, and chemotherapeutics.	DUKE
Anti-helmintic	33281	An agent that kills or expels parasitic worms, treating helminthic infections. Therapeutically, it targets intestinal parasites, reducing infection symptoms. Key medical uses include treating roundworm, hookworm, and tapeworm infections.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti-cancer	35610	An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.	DUKE
Anti-fatigue	52217	An agent that reduces physical and mental exhaustion, enhancing endurance and vitality. It plays a biological role in regulating energy metabolism and mitigating oxidative stress. Therapeutically, anti-fatigue agents are used to manage chronic fatigue syndrome, improve athletic performance, and alleviate symptoms of anemia and other debilitating conditions.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti leukemic	35610	An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti peroxidant		An agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging.	DUKE
Anti radicular		An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-sickling		An agent that prevents sickling of red blood cells, used to treat sickle cell anemia by reducing hemoglobin polymerization and improving blood flow, thereby alleviating associated pain and complications.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Antitumor promoter	35610	An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.	DUKE
Ascaricide	33281	An agent that kills roundworms, particularly Ascaris species, playing a crucial role in treating parasitic infections. Therapeutically, it is used to eliminate intestinal parasites, reducing the risk of complications. Key medical uses include treating ascariasis, a common intestinal infection, and preventing related conditions such as malnutrition and intestinal blockages.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Choleretic		An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Immunosuppressant	35705	An agent that suppresses the immune system, reducing inflammation and preventing rejection in organ transplants, and treating autoimmune diseases such as rheumatoid arthritis and lupus.	DUKE
Laxative	50503	An agent that stimulates bowel movements, relieving constipation by softening stool or increasing intestinal motility. Therapeutically, laxatives are used to treat constipation, prepare the bowel for medical procedures, and manage certain medical conditions, such as irritable bowel syndrome.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Ubiquiot		An antioxidant that protects cells from damage, playing a crucial role in energy production. Therapeutically, it has applications in managing neurodegenerative and cardiovascular diseases, with key medical uses including reducing oxidative stress and improving mitochondrial function.	DUKE

Enzymes

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Metabolism and Physiological Effects of Vanillic Acid	SMP0126881	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
dairy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
milky	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
creamy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bean	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.